Water → 2-(4-Cyanophenyl)propanoic acid

HRID 1428792Notes

Reaction equation

HRID 1428792 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]([CH3:15])[C:10]([O:12]CC)=[O:11])=[CH:5][CH:4]=1)#[N:2].O1CCCC1.O.[OH-].[Na+]>C(OC(=O)C)C.C(O)(=O)C>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([CH:9]([CH3:15])[C:10]([OH:12])=[O:11])=[CH:7][CH:8]=1)#[N:2]

Participants

7

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 4550989Ethyl 2-(4-cyanophenyl)propanoate

Product 1

HCID 225698632-(4-Cyanophenyl)propanoic acidYield 122.4%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of ethyl 2-(4-cyanophenyl)propanoate (453 mg, 1.968 mmol) in co-solvent with tetrahydrofuran and water (1:1) were added sodium hydroxide (197 mg, 4.919 mmol). The reaction mixture was stirred for overnight at room temperature, then acidified to pH 3-4 with acetic acid. The residue was diluted with ethylacetate and washed with water and brine. The organic layer was dried over magnesium sulfate and filtered. The filtrate removed in vacuo. The crude 2-(4-cyanophenyl)propanoic acid (422 mg) was obtained as 99% yield.

Workup

  1. washwashed with water and brine
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. filtrationfiltered
  4. customThe filtrate removed in vacuo

Sources & evidence

ORD record
ord-c6e50572f0244bedbd2cfc9322caee9b
Source dataset
uspto-grants-2015_01
Patent number
US08937092B2

Reaction notes

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